ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
γ-Lactones from α, β-Unsaturated Ketones by P—O OlefinationThe enones 2-5, 12, 14, 16-19 react with the phosphonate 1b in moderate to good yields to the E,Z-esters 6-9, 13, 15, 20-23. The γ, δ double bond of Z-8 was epoxidized to Z-31, which was hydrolyzed with acid to the butenolide 34. 34, and all the other γ-lactones 32, 33, 41, 44 are prepared in much better yields by P-O olefination of the epoxy ketones 26-28, 38, 42 to the E,Z-esters 29-31, 39, 43 followed by hydrolysis of the Z-esters. The E-esters 30, 31, 39 are hydrolyzed to the trans-diols 35, 36, and 40.
Notes:
Die Enone 2-5, 12, 14, 16-19 reagieren mit dem Phosphonat 1b in mäßigen bis guten Ausbeuten zu den E,Z-Estern 6-9, 13, 15, 20-23. Aus Z-8 wird durch Epoxidierung der γ,δ-Doppelbindung Z-31 und daraus nach saurer Hydrolyse das Butenolid 34 erhalten. 34 und alle weiteren γ-Lactone 32, 33, 41, 44 sind in erheblich besseren Ausbeuten durch P—O-Olefinierung der Epoxyketone 26-28, 38, 42 zu den E,Z-Estern 29-31, 39, 43 und Hydrolysieren der Z-Ester darstellbar, während die E-Ester 30, 31, 39 die trans-Diole 35, 36 und 40 liefern.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19791120632
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